


Taking Turns

by CS_impala67



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean Winchester, Caring Castiel (Supernatural), Confused Castiel (Supernatural), First Time Bottom Dean Winchester, First Time Bottoming, Gentle Castiel (Supernatural), M/M, Nervous Dean Winchester, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2019-02-19
Updated: 2019-02-19
Packaged: 2019-10-31 17:17:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,662
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17853833
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: Dean was nervous. He had always topped with Castiel. But he couldn’t help feeling curious about how it would feel to bottom.





	Taking Turns

Castiel and Dean walked into Cas’ apartment. Dean was nervous. Which is not like him. He is normally the confident one, especially in the bedroom. He always tops. He is the dominant one. But that's why he was so nervous. They have been together for a year now and having sex pretty much just as long. It was amazing. But Dean only ever got to feel what it was like to be on top. Not that he minded that so much. He freaking loved it! Cas always felt so good to be inside. 

But Dean was curious. He wanted to know what it felt like for Castiel. He guessed it felt pretty damn good from the sounds his boyfriend always made. Dean wanted to feel it at least once since he had never bottomed before. He was always too scared to. He kind of looked at it as being a rite of passage per se. He knew that was stupid. Not every gay man took it up the ass. There were plenty who only topped. And some who didn’t even like anal at all. But he still thought he should experience it at least once. He was nervous as hell though! He felt embarrassed and shy at the thought of even asking Cas to top him. Castiel bottoming was always just assumed. The first time they had sex it just happened that way, he guessed with Dean being the more dominant one, they both just went with the flow. So now to ask his boyfriend to switch roles felt awkward. What was he gonna say? " Hey Cas babe, can you please fuck me in the ass this time?" Yeah, because that didn't sound stupid, Winchester. Maybe he could just figure it out on the fly. 

" Dean, babe lets go to bed. We had a long day." Cas said, as he faked a yawn. Yeah he wasn't tired. That was his way of saying he wanted some fun time. 

" Yeah sure thing." Dean replied with a knowing smirk.

They went to the bedroom and as soon as Cas shut the door, Dea grabbed him by the waist and pulled him to his chest. Their lips crashed together as they both fought for dominance. Usually Dean always won, but he let Cas get the upper hand this time. Cas must have been surprised because he paused for a second before continuing. Dean was hoping if he gave him control, then Cas would take him this time. 

Cas’ tongue explored Dean’s mouth and he moaned against his lips. They stumbled toward the bed and stopped kissing long enough to pull their shirts off. Then their lips came together again and bare chests touched. His lover’s skin felt like fire touching Dean. He could feel his dick get hard through my pants. Cas felt his hand all the way down Dean’s chest and when he reached his pants he grabbed his erection through his jeans. Dean gasped and moaned into his mouth. He started kissing Dean’s neck and he found the soft spot right behind his ear that always send a spark down to his groin. He moaned so loud. Cas smiled against his skin and continued to kiss down his neck to his chest and licked all the way down as he got to his knees in front of Dean. He undid his pants and ripped then down along with his boxers so Dean was completely naked in front of him. He grabbed Dean’s dick and began massaging it before he took it in his mouth. Dean cried out, it felt so good. He went faster making Dean feel so good. His lover stopped before he could climax, knowing they both didn't want it to end there. He stood up and stripped out of his clothes and they both got into bed. Cas was laying on top of Dean and they kissed so fiercely they were panting. 

Castiel reached over to the nightstand to get a condom. He opened it and was about to put it on Dean but he stopped him.

" Don't you want to have sex?" Cas asked his boyfriend, confused.

" Of course I do" Dean replied. 

" Well then, I need to put this on you. I'm not going bareback." Cas said, starting to get frustrated. 

"Of course we’re gonna use a condom, but I don't want it on me though." 

" Well how are we gonna have sex with one if you don't let me put it on you?" Cas asked, annoyance clear in his tone. 

" I want you to wear it."

" How will me wearing a condom make any sense if you are gonna fuck me?" he asked as if Dean was stupid. He didn't understand what was being implied. Castiel didn’t always get subtlety. 

" Because I'm not gonna fuck you." Dean said, as his ears started turning red. Ugh. Why couldn’t Cas just understand what he was hinting at! This would be so much easier. 

" What do you mean? You just said we were gonna have sex. And now you are saying you aren't gonna fuck me. You’re confusing me." 

" I'm not gonna fuck you because..." Dean tried to get the words out. 

" Because what?" he asked getting more annoyed. 

" Because I want you to fuck me." Dean rushed out, said closing his eyes. He was embarrassed. 

" Wait. What?" he asked

" I want you to be inside me this time. I want to be the bottom. I want to experience the way you feel when I fuck you. I want to know what it's like." 

" Oh wow! I never thought you would ever ask that. You always seemed to like the top. But if you want to switch tonight I would love to. I've never got to experience that either."

" okay good. Just...go slow okay? I know it's gonna hurt so just be gentle with me." Dean asked weakly

" Of course baby. I would never hurt you. This is your first time. I'm gonna go slow. I'm gonna make love to you baby." he said as he kissed his shy lover. " well we don't need the condom yet, I have to prepare you first." he said. He moved down between Dean’s legs and started sucking him again. All of a sudden Dean felt a finger at his entrance and braced himself. 

" Relax baby. If you tense up it will hurt more." He relaxed and felt a finger go inside him. It hurt a little but he could take it. Cas started pushing it in and out of him and then he slipped another finger in. It hurt, him stretching his hole like that. He was about to tell him to stop when all of a sudden, Dean’s back arched and He let out a scream of pleasure. 

" oh my god what the hell did you just do?" He asked him. 

" I hit your prostate. That's a man’s best friend. Felt amazing right?" 

" fuck yes! Don't stop." 

He gently took his fingers and trusted then into his boyfriend again. He moaned in so much pleasure. He couldn't take it anymore. He wanted to feel Cas inside him right now. 

" Cas, I'm ready." 

Cas climbed up and kissed him. He put the condom on and positioned himself at his boyfriend’s virgin entrance.

" Just relax baby. I'm gonna go slow okay. It might hurt a little at first. But it will get so much better." he said. And then he started pushing his head inside of Dean’s ass. There was a sharp jolt of pain and a few tears leaked out his eyes. Cas kissed them softly. 

" Baby look at me. I'll stop if you want. We don't have to do this." 

" No I want this. I really do." Dean breathed out, breath ragged. 

Cas pushed in a little further and it hurt so bad. He didn't know how Cas took this all the time. Once the pain started to go down, Cas pushed further and almost thrusted all the way in.

" ahhhhh. Oh my god this hurts so bad. I don't think I can do this." Dean cried.

" If you want me to pull out I will. But I know how much you wanted to try. The first time is always the hardest. I promise it gets better. Just tell me what you want baby. I have no problem stopping, my love." he said as he kissed the tears

" Just, just don't move yet." Dean said. Slowly he started to relax and told Cas so. His boyfriend pulled out a little and pushed back in. Then again. And again. The pain started to go way and pleasure started to take over. He pulled out and thrusted in Dean and hit that spot again. 

" Cas, Castiel!...oh god, please fuck me." He screamed surprising both Cas and himself.

Cas started picking up speed and really thrusting into Dean hard, hitting that spot every time. He thought he had died and went to heaven. He screamed and moaned so loud. He couldn't take the pleasure anymore and shot his load all over his chest. He didn’t even know he could cum without touching his cock!

" Holy shit that was amazing. I've never felt that much pleasure in my life. I came not even touching my cock." He said

" That was pretty hot. I've never even don't that. So I'm guessing you liked being the bottom?" he asked Dean as he pulled out and flopped down beside him.

" Hell yes! no wonder you love it so much. " 

" Being on top was amazing too." Cas replied. 

" So I guess we will be taking turns from now on?" Dean asked with a smile. 

“Anything you want my love. It will be nice to switch it up.”

“Love you Cas”

“Love you too Dean.”

 

Dean laid his head on Cas’ chest as they drifted off to sleep. He knew he’d regret not cleaning up when he woke up. But he was too tired and fucked out to care.

**Author's Note:**

> If you see any grammar mistakes, please let me know! I originally wrote this as a first person story but decided to change it. So if you see something I missed let me know! And thank you for reading!


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